Upper West Side New York, NY

Originally inhabited by Native Americans, the land that comprises the Upper West Side received the name Bloomingdale (valley of the flowers) after Dutch immigrants settled it in the early- to mid-1600s. For the next few centuries Bloomingdale remained countryside, with farms and rolling hills producing crops such as tobacco. Residential buildings continued to sprout up over time, lending a more urban feel to an area that still felt cut off from the city proper. Not until the late 19th century did a construction boom first hit the area. Between 1885 and 1910, developers completed numerous high-rise residential buildings, including the famous Dakota at Central Park West.

The relocation of Columbia University from midtown to the West 110s and the arrival of the subway in 1904 also increased traffic and access to the neighborhood. Diverse populations settled in the area during the subsequent decades, with the most expensive housing along Central Park and the lower-rent housing along Amsterdam Avenue.

In the 1970s and '80s, gentrification caused a significant hike in property values and encouraged new construction. One of the treasures of the Upper West Side today is the Museum of Natural History, which attracts five million visitors each year and employs a full-time scientific staff of more than 200 people. Its vast collection of artifacts contains everything from pre-Columbian burial urns to a hall of meteorites.

Although not at the heart of New York City's flashy, internationally known culinary scene, the Upper West Side contains scores of cozy neighborhood restaurants, especially along Amsterdam Avenue. Night owls can find low-key nightlife in area bars, but true partiers tend to travel downtown before returning home to quieter streets. An Upper West Side institution for more than a century, Barney Greengrass serves as a restaurant and deli on Amsterdam Avenue near West 87th Street. Diners flock here in particular for brunch, which features bagels topped with salmon, eggs with a side of sturgeon. Barney Greengrass has also maintained a presence in popular culture; the Tom Hanks film "Extremely Loud and Incredibly Close" includes five scenes shot on the premises. One of the trendiest spots around, Jacob's Pickles, offers killer cocktails and beer flights that complement southern-inspired fare and plenty of house-made pickles. Try the deep fried pickles with crunchy breading, and wash them down with the Spicy Brine Margarita featuring house-infused jalapeno tequila. If you're looking for top-notch cuisine with a casual flare, head to Bar Boulud near Lincoln Center. The menu features seasonal French bistro fare, with charcuterie, terrines and pates to please the most sophisticated meat lovers. Diners in the know also recommend the seafood dishes, including the classic steamed mussels with bacon and grilled sourdough. Bar Boulud fills up with Lincoln Center ticketholders in the early evenings, who cross the street after dinner to see world-class ballet, opera and theater performances.

While you could happily spend the majority of your waking hours on the Upper West Side, stumbling upon new bakeries and design boutiques every block, extensive and reliable mass transit systems make for easy access to the rest of the city. The Metropolitan Transportation Authority operates a 24-hour subway system, and seven train lines (1, 2, 3, A, B, C and D) run through the neighborhood. The stations at Broadway and 72nd and Broadway and 96th Streets act as hubs for commuters switching from express lines to local trains or cross-town buses. Numerous buses also run parallel to the subway in a north-south direction, adding yet another transport option.

In warmer months bicycles prove popular. A bike lane on Columbus Avenue offers quick passage through the heart of the neighborhood, while long-distance bikers can head to Riverside Park, where a paved path runs south to 59th Street and connects with the Hudson River Park Bikeway, the busiest such bikeway in the United States.

With a high population density and popularity with New Yorkers and out-of-towners alike, driving a car in the neighborhood is not recommended. Car owners can find street parking, but competition is steep, and weekly street cleaning means you can’t leave your car unattended for long. Parking garages also exist for those willing to pay.

Upper West Siders have unparalleled access to some of the most treasured urban green spaces on the planet. Originally opened in 1857, Central Park now covers 843 acres between 59th and 110th streets, with Central Park West defining the neighborhood’s eastern border. The park features miles of walking, jogging and biking paths, as well as athletic facilities, scenic bodies of water and a small urban zoo. Every summer, residents and tourists alike line up by the hundreds to attend Shakespeare in the Park, a series of free performances held outdoors at the Delacorte Theater.

At the western edge of the neighborhood, the lesser-known but no less beautiful Riverside Park runs along the Hudson. It features breathtaking views of the river and a quieter vibe than its neighbor to the east. Every summer the entirety of the park plays host to Summer on the Hudson, an outdoor festival featuring events such as music concerts, dance performances and wellness activities.

The cost of living on the Upper West Side skews higher than New York City at large. Renters can find one-bedroom apartments for as low as $1,600 in the older mid-rise buildings along Amsterdam Avenue, but such gems are rare and rents increase exponentially from there. The overall desirability of the neighborhood and high commercial rents drive prices for groceries and other everyday items higher. However, residents would point out the walkability of the neighborhood cuts back on transportation costs, and the convenience of amenities is priceless.

Though not known as a shopping destination to outsiders, the Upper West Side offers a wide range of shopping options. Clothing store chains such as Zara and Banana Republic coexist with tiny art galleries and bookstores alike. For a true literary fix, head north of the 72nd Street subway station on Broadway to Westsider Rare Books. This independently owned bookstore features used and rare finds, all packed from floor to ceiling inside a cozy retail space.

On Amsterdam Avenue at West 94th Street, the Little Shop of Crafts has made a name for itself as a destination for everything from children’s birthday parties to date nights. This interactive craft store allows visitors to create their own art, including pottery, woodcraft and T-shirts. With an enthusiastic staff and free wine on weekend evenings, the whole family can get in on the fun.

Residents seeking groceries and everyday items find options on nearly every block and for a range of budgets, including chains like Associated, Whole Foods and Trader Joe's. Food lovers in search of farm-fresh fare can head to one of the 79th Street and 97th Street Greenmarkets, open year-round on Sundays and Fridays, respectively.